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Direct Observation of a Cationic Gold(I)–Bicyclo[3.2.0]hept‐1(7)‐ene Complex Generated in the Cycloisomerization of a 7‐Phenyl‐1,6‐enyne
Author(s) -
Brooner Rachel E. M.,
Brown Timothy J.,
Widenhoefer Ross A.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201301640
Subject(s) - cycloisomerization , enyne , ene reaction , cationic polymerization , bicyclic molecule , chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The reaction of enyne 1 with a 1:1 mixture of [LAuCl] and AgSbF 6 in CD 2 Cl 2 at −20 °C gave the gold complex 2 in 97 % yield (NMR spectroscopy). Warming a solution of 2 at 25 °C led to 1,3‐H migration ( t 1/2 ≈16 min) to form the gold complex 3 with 96 % selectivity. 13 C NMR analysis of 2 and 3 showed predominant metallacyclopropane character of the goldbicyclo[3.2.0]heptene bond.